N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 2-phenylpyrrolidine-1-carboxylate

HRID 321949ノート

反応式

HRID 321949 の反応式
CN(C)CCN(C)C.[Li]CCCC.[C:14]([N:21]([CH2:29][CH2:30][CH2:31]Cl)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C1COCC1>[C:17]([O:16][C:14]([N:21]1[CH2:29][CH2:30][CH2:31][CH:22]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

参加物

5

反応物 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11098062N-Boc-N-benzyl-3-chloropropylamineHCID 178418339Butyllithium

生成物 1

HCID 3772557Tert-butyl 2-phenylpyrrolidine-1-carboxylate収率 65.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield).

後処理

  1. customThe reaction mixture was then quenched with aqueous NH4Cl (20 mL)
  2. additiondiluted with Et2O (150 mL)
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted twice with Et2O
  5. washThe combined organic phases were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

出典と根拠

ORDレコード
ord-f7cffdb1601b4147957e2c4ae980b705
出典データセット
uspto-grants-2001_04
特許番号
US06211170B1

反応ノート

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